Unique Superbase TBD (1,5,7-Triazabicyclo[4.4.0]dec-5-ene): From Catalytic Activity and One-Pot Synthesis to Broader Application in Industrial Chemistry

Abstract

TBD (1,5,7-triazabicyclo[4.4.0]dec-5-ene) is an organic superbase with unique catalytic effects due to its bifunctionality. It is already successfully used as a versatile catalyst, e.g., for transesterification, amidation, Michael addition, and aldol reactions, in technical silicone chemistry and even for enantioselective transformations. Currently, main applications are in innovative polymer chemistry (vitrimers, nonisocyanate polyurethanes, and polyureas). Restrictions of a broader application of TBD in technical processes due to its limited market availability and the complicated handling of its crystalline delivery form are now overcome by a simple one-pot synthesis of TBD, which generates an easy-to-make, ready-to-apply liquid formulation.

New Horizon in Phospha-Michael Reaction: Ultrafast Double Addition of P–H Bond-Bearing Nucleophiles to Electron-Deficient Triple Bonds and Its Use for Functional Monomer Synthesis and Polymer Modification

“…Within the scope of this work, we preferred TBD as the catalyst due to its outstanding performance in Michael reactions. [33][34][35][36][37]51,52 Finally, for simplicity, the parametric studies were conducted by using DMAD, and the results obtained from these studies are collected in Table 2.…”

“…An extended and much more detailed parametric study is still in progress, and the effects of other parameters are part of another ongoing study. Within the scope of this work, we preferred TBD as the catalyst due to its outstanding performance in Michael reactions. − ,, Finally, for simplicity, the parametric studies were conducted by using DMAD, and the results obtained from these studies are collected in Table .…”

Triazabicyclodecene: A versatile catalyst for polymer synthesis

“…Unlike inorganic bases, the lipophilic organic TBD is soluble in organic media and can participate in various organic transformations. [1][2][3] It exhibits a unique chemical ability to act as both a proton donor and acceptor, distinguishing it from other superbases. 4 Its synthesis was initially reported by McKay in 1957, 5,6 and its catalytic activity has been investigated for esterification, [7][8][9] amidation, 10,11 Michael reactions, 12,13 aldol reaction, 14 epoxidation, 15 and the Wittig reaction.…”

“…1,5,7‐Triazabicyclo[4,4,0]dec‐5‐ene (TBD) is a bicyclic superbase with a guanidine skeleton and a high pK BH+ value of 26.0 (Scheme 1). Unlike inorganic bases, the lipophilic organic TBD is soluble in organic media and can participate in various organic transformations 1–3 . It exhibits a unique chemical ability to act as both a proton donor and acceptor, distinguishing it from other superbases 4 .…”

Metal-free recycling of waste polyethylene terephthalate mediated by TBD protic ionic salts: the crucial role of anionic ligands

“…34 In recent years, metal-free glycolysis has emerged as an environmentally friendly approach for recycling PET (as shown in Scheme 1). [34][35][36][37][38][39][40][41] Among the various metal-free catalysts, 1,5, 7-triazabicyclo[4.4.0]dec-5-ene, an organic base with Brønsted acidic N-H groups and a pK a value of 26.03, 42,43 has been utilized in the transesterification reaction. 44,45 In 2011, Kazuki Fukushima pioneered the use of TBD in PET glycolysis and achieved a yield of 78% of BHET at a temperature of 190 1C for 3.5 hours.…”